Hydrochloric Acid → HCID 68410798, compound

HRID 2194719Notes

Reaction equation

HRID 2194719 reaction equation
[C:1]1([C:7]2[N:8]([C:14]3[N:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH:9]=[C:10]([CH:12]=O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][NH2:21].CO.[BH4-].[Na+].[ClH:26].C(=O)([O-])O.[Na+]>CO>[ClH:26].[ClH:26].[CH3:20][NH:21][CH2:12][C:10]1[N:11]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]([C:14]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:9]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 86644404HCID 86644404, compound

Product 1

HCID 68410798HCID 68410798, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-phenyl-1-pyrimidin-2-yl-1H-imidazole-4-carbaldehyde (150 mg) in methanol (15 mL) was added 40% methylamine-methanol solution (233 mg) and the mixture was stirred for 10 min. Sodium borohydride (68 mg) was added and the mixture was stirred for 10 min. 1 mol/L Hydrochloric acid was added to the reaction mixture and the mixture was stirred for 30 min. The mixture was neutralized with saturated sodium hydrogen carbonate solution, and extracted with tetrahydrofuran. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:ethyl acetate-methanol=19:1→7:3) and dissolved in methanol (5 mL). A 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added, and the mixture was concentrated under reduced pressure. Tetrahydrofuran was added to the residue, and insoluble materials were collected by filtration to give the title compound as a colorless powder (yield 55 mg, yield 27%).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. stirringthe mixture was stirred for 30 min
  3. extractionextracted with tetrahydrofuran
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (eluent:ethyl acetate-methanol=19:1→7:3)
  7. dissolutiondissolved in methanol (5 mL)
  8. additionA 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added
  9. concentrationthe mixture was concentrated under reduced pressure
  10. additionTetrahydrofuran was added to the residue, and insoluble materials
  11. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-998db2ca70c944ffa86b5043a664c53a
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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